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Broadly speaking, the spots are still the same.
Post college: Lincoln Park, Lakeview (and Wrigleyville), River North, Wicker Park are still the spots to be if you've got a good income.
West Loop is a newer entrant in the trendy neighborhoods, but doesnt have the older housing stock that allows for some cheaper starting out options. And the Wicker Park vibe has expanded into Bucktown, and parts of Humboldt Park and Logan Square if hes more into the alternative scene.
Will he need roommates? Probably not. Will he want roommates to get the best spot? Probably, at least while establishing himself.
Spot for what? Sure it’s a great spot but you also need to consider interests and commute
River North
He’s gonna work in the loop for a consulting firm. I dunno he’s your basic 22 year old guy. Big 10 school. Likes sports.
He may like wrigleyville as well
River North or Old Town
It’s still Lincoln Park